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Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-07 16:24:12 UTC |
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HMDB ID | HMDB0000224 |
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Secondary Accession Numbers | - HMDB0012279
- HMDB00224
- HMDB0060151
- HMDB0060152
- HMDB12279
- HMDB60151
- HMDB60152
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Metabolite Identification |
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Common Name | O-Phosphoethanolamine |
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Description | O-Phosphoethanolamine, also known as PEA, phosphorylethanolamine, colamine phosphoric acid or ethanolamine O-phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine is used in the biosynthesis of two different types of phospholipids: glycerophospholipids and sphingolipids. O-Phosphoethanolamine exists in all living species, ranging from bacteria to plants to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine; which is mediated by the enzyme ethanolamine-phosphate cytidylyltransferase. In addition, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is catalyzed by the enzyme choline/ethanolamine kinase. In humans, O-phosphoethanolamine is involved in phosphatidylcholine biosynthesis. O-phosphoethanolamine is also a product of the metabolism of sphingolipids. In particular, sphinglipids are metabolized in vivo to phosphorylethanolamine and a fatty aldehyde, generally palmitaldehyde. Both metabolites are ultimately converted to glycerophospholipids. The lipids are first phosphorylated by a kinase and then cleaved by the pyridoxal-dependent sphinganine-1-phosphate aldolase. Elevated urine levels of O-Phosphoethanolamine or PEA can be used to help in the diagnosis of Hypophosphatasia (HPP). Reference ranges for urinary PEA vary according to age and somewhat by diet, and follow a circadian rhythm. Outside of the human body, O-phosphoethanolamine has been detected, but not quantified in, several different foods, such as oxheart cabbages, anises, shiitakes, abalones, and teffs. |
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Structure | InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6) |
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Synonyms | Value | Source |
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2-Amino-ethanol dihydrogen phosphate | ChEBI | 2-Amino-ethanol phosphate | ChEBI | Colamine phosphate | ChEBI | Colamine phosphoric acid | ChEBI | Colaminphosphoric acid | ChEBI | EAP | ChEBI | Ethanolamine acid phosphate | ChEBI | Ethanolamine O-phosphate | ChEBI | Ethanolamine phosphate | ChEBI | mono(2-Aminoethyl) phosphate | ChEBI | Monoaminoethyl phosphate | ChEBI | O-Phosphocolamine | ChEBI | O-Phosphorylethanolamine | ChEBI | OPE | ChEBI | PE | ChEBI | PEA | ChEBI | PETN | ChEBI | Phosphoethanolamine | ChEBI | Phosphoric acid 2-aminoethyl phenyl ester | ChEBI | Phosphoryl-ethanolamine | ChEBI | 2-Amino-ethanol dihydrogen phosphoric acid | Generator | 2-Amino-ethanol phosphoric acid | Generator | Colaminphosphate | Generator | Ethanolamine acid phosphoric acid | Generator | Ethanolamine O-phosphoric acid | Generator | Ethanolamine phosphoric acid | Generator | mono(2-Aminoethyl) phosphoric acid | Generator | Monoaminoethyl phosphoric acid | Generator | Phosphate 2-aminoethyl phenyl ester | Generator | Phosphonoethanolamine | HMDB | 2-Amino-ethanol dihydrogen phosphate (ester) | HMDB | 2-Aminoethanol O-phosphate | HMDB | 2-Aminoethyl dihydrogen phosphate | HMDB | 2-Aminoethyl dihydrogen phosphate (acd/name 4.0) | HMDB | 2-Aminoethyl phosphate | HMDB | Colamine acid phosphate | HMDB | Colaminephosphoric acid | HMDB | Ethamp | HMDB | O-Phosphonatoethanaminium | HMDB | Phosphoryethanolamine | HMDB | Phosphorylethanolamine | HMDB | Phosphorylethanolamine, 3H-labeled CPD | HMDB | Phosphorylethanolamine magnesium (1:1) salt | HMDB | Phosphorylethanolamine zinc salt | HMDB | Phosphorylethanolamine, cobalt (2+) (1:1) salt | HMDB | Calcium 2-aminoethanol phosphate | HMDB | Phosphorylethanolamine ca (1:1) salt | HMDB |
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Chemical Formula | C2H8NO4P |
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Average Molecular Weight | 141.063 |
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Monoisotopic Molecular Weight | 141.019094261 |
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IUPAC Name | (2-aminoethoxy)phosphonic acid |
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Traditional Name | phosphorylethanolamine |
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CAS Registry Number | 1071-23-4 |
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SMILES | NCCOP(O)(O)=O |
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InChI Identifier | InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6) |
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InChI Key | SUHOOTKUPISOBE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Organic phosphoric acids and derivatives |
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Sub Class | Phosphate esters |
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Direct Parent | Phosphoethanolamines |
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Alternative Parents | |
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Substituents | - Phosphoethanolamine
- Monoalkyl phosphate
- Alkyl phosphate
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect
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Adverse health effect
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Disposition
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Biological location
Source
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Process
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Naturally occurring process
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 241 - 243 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 72 mg/mL | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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O-Phosphoethanolamine,1TMS,isomer #1 | C[Si](C)(C)OP(=O)(O)OCCN | 1444.3 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,1TMS,isomer #1 | C[Si](C)(C)OP(=O)(O)OCCN | 1352.1 | Standard non polar | 33892256 | O-Phosphoethanolamine,1TMS,isomer #1 | C[Si](C)(C)OP(=O)(O)OCCN | 2301.6 | Standard polar | 33892256 | O-Phosphoethanolamine,1TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O | 1553.1 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,1TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O | 1437.8 | Standard non polar | 33892256 | O-Phosphoethanolamine,1TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O | 2505.0 | Standard polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C | 1457.0 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C | 1452.6 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C | 1924.0 | Standard polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C | 1565.4 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C | 1550.1 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #2 | C[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C | 1960.5 | Standard polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #3 | C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C | 1736.4 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #3 | C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C | 1657.1 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TMS,isomer #3 | C[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C | 2391.9 | Standard polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #1 | C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 1591.7 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #1 | C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 1635.6 | Standard non polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #1 | C[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 1676.1 | Standard polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #2 | C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C | 1751.0 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #2 | C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C | 1730.0 | Standard non polar | 33892256 | O-Phosphoethanolamine,3TMS,isomer #2 | C[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C)[Si](C)(C)C | 1919.3 | Standard polar | 33892256 | O-Phosphoethanolamine,4TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1773.0 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,4TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1771.1 | Standard non polar | 33892256 | O-Phosphoethanolamine,4TMS,isomer #1 | C[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C | 1708.5 | Standard polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN | 1680.4 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN | 1557.0 | Standard non polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN | 2374.9 | Standard polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O | 1791.8 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O | 1654.2 | Standard non polar | 33892256 | O-Phosphoethanolamine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O | 2611.2 | Standard polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C | 1910.7 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C | 1852.8 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN)O[Si](C)(C)C(C)(C)C | 2068.7 | Standard polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C | 1996.9 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C | 1991.4 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O)O[Si](C)(C)C(C)(C)C | 2182.2 | Standard polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C | 2128.3 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C | 2071.8 | Standard non polar | 33892256 | O-Phosphoethanolamine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCOP(=O)(O)O)[Si](C)(C)C(C)(C)C | 2485.1 | Standard polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2224.0 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2205.0 | Standard non polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2045.2 | Standard polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2379.9 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2327.9 | Standard non polar | 33892256 | O-Phosphoethanolamine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OP(=O)(O)OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2216.7 | Standard polar | 33892256 | O-Phosphoethanolamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2601.2 | Semi standard non polar | 33892256 | O-Phosphoethanolamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2483.1 | Standard non polar | 33892256 | O-Phosphoethanolamine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OP(=O)(OCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2130.0 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0fki-0910000000-63541b89e6730018e48b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-MS (4 TMS) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Non-derivatized) | splash10-0fki-0910000000-63541b89e6730018e48b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) | splash10-0h9a-1921000000-3a1d4ab89b928259f71d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - O-Phosphoethanolamine GC-EI-TOF (Non-derivatized) | splash10-0fki-0911000000-7fc066f17e2ebf6c84f8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) - 70eV, Positive | splash10-000t-9100000000-543d2d90aa663406e999 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - O-Phosphoethanolamine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-88dc3b66f275af50de34 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-0006-2900000000-9cf72ee86018eb78504f | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-004i-9000000000-169b03f94a9f53bd0de4 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-004i-9000000000-199d7ab7a4aeb040674e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-004i-9000000000-f573b62dada3630598c3 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-004i-9000000000-38c04ce07a85a8db342c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-004i-9100000000-b582c6b51602884756da | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF | splash10-0006-2900000000-9cf72ee86018eb78504f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF | splash10-004i-9000000000-169b03f94a9f53bd0de4 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF | splash10-004i-9000000000-199d7ab7a4aeb040674e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF | splash10-004i-9000000000-f573b62dada3630598c3 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QQ , negative-QTOF | splash10-004i-9000000000-38c04ce07a85a8db342c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine LC-ESI-QTOF , negative-QTOF | splash10-004i-9100000000-b582c6b51602884756da | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine , negative-QTOF | splash10-004i-9000000000-4335e927ba2537543f7d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine , negative-QTOF | splash10-004i-9000000000-3e5f10c6e140e555b9fe | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 40V, Negative-QTOF | splash10-004i-9000000000-db65ce46b55b09e54fd2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 20V, Negative-QTOF | splash10-004i-9000000000-2fd2f3cd8548fd78801d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Negative-QTOF | splash10-004i-9000000000-f56d20ee0f56f087220d | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 35V, Negative-QTOF | splash10-004i-9000000000-d64f2b030ca512262fb1 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-0006-9100000000-993b8efd11624567ec4b | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-0006-9000000000-f2fd3c258685af07afb5 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0006-9000000000-b479823e7c0ee6b5e03d | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 40V, Positive-QTOF | splash10-0006-9000000000-c4e1a40502d86192ed6b | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Positive-QTOF | splash10-0006-9000000000-b5f55e00526c703b9bed | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 20V, Positive-QTOF | splash10-0006-9000000000-e5987c09032f652371ca | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - O-Phosphoethanolamine 10V, Positive-QTOF | splash10-0006-9000000000-42653da62fb10227ae1b | 2021-09-20 | HMDB team, MONA | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 19 +/- 9.9 uM | Newborn (0-30 days old) | Both | Normal | | details | Blood | Detected and Quantified | 4.0 +/- 2.0 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6.0 +/- 1.1 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 6.30 (4.70-9.60) uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 50.9 +/- 34.1 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 66.2 +/- 20.4 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 76.2 +/- 64.8 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 14.8 +/- 17.4 uM | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 30.53 +/- 32.79 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | <9.95 umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0-53 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 142.263 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <5.43 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 1.69-38.57 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 3.73-38.69 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 4.276 (1.644-6.908) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 2.15-18.55 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 8.2 +/- 2.0 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | - Geigy Scientific ...
- West Cadwell, N.J...
- Basel, Switzerlan...
| details | Urine | Detected and Quantified | <25 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 1.36-13.35 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 7.91 +/- 18.09 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 10.18 +/- 12.44 umol/mmol creatinine | Newborn (0-30 days old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 11.3 (6.50-16.4) uM | Adult (>18 years old) | Both | Brain injury | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Attachment loss | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | Urine | Detected and Quantified | 71.48 +/- 35.869 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 84 umol/mmol creatinine | Children (1-13 years old) | Female | Odontohypophosphatasia | | details |
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Associated Disorders and Diseases |
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Disease References | Traumatic brain injury |
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- Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
| Crohn's disease |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Eosinophilic esophagitis |
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- Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
| Odontohypophosphatasia |
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- Haliloglu B, Guran T, Atay Z, Abali S, Mornet E, Bereket A, Turan S: Infantile loss of teeth: odontohypophosphatasia or childhood hypophosphatasia. Eur J Pediatr. 2013 Jun;172(6):851-3. doi: 10.1007/s00431-012-1868-4. Epub 2012 Oct 24. [PubMed:23093139 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB01738 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031115 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 990 |
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KEGG Compound ID | C00346 |
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BioCyc ID | PHOSPHORYL-ETHANOLAMINE |
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BiGG ID | 1485304 |
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Wikipedia Link | Phosphorylethanolamine |
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METLIN ID | 5233 |
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PubChem Compound | 1015 |
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PDB ID | Not Available |
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ChEBI ID | 17553 |
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Food Biomarker Ontology | Not Available |
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VMH ID | ETHAMP |
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MarkerDB ID | MDB00000106 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Muller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [PubMed:12097436 ]
- Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. [PubMed:15756940 ]
- Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
- Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. [PubMed:7791524 ]
- Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. [PubMed:8588821 ]
- Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. [PubMed:11566853 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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